Process of making hydroxy stearic acid.



Patented October 11, 1904.

NITED STATES PATENT OFFICE.

WILLIAM M. BURTON, OF CHICAGO, ILLINOIS, ASSIGNOR TO STANDARD OILCOMPANY, OF CHICAGO, ILLINOIS, A CORPORATION OF INDIANA.

PROCESS OF MAKING HYDFIOXY STEARIC ACID.

SPECIFICATION forming part of Letters Patent No. 772,129, dated October11, 1904. Application filed August 12, 1904:. Serial No. 220,533. (N0specimens.)

To all whom it may concern.-

Be it known that I, WILLIAM M. BURTON, a citizen of the United States,residing at Chicago, in the county of Cook and State of Illinois, haveinvented a new and useful Process of Manufacturing H ydroxy Stearic Acidfrom Oleic Acid, of which the following is a specification.

My invention relates to an improved pro' cedure inthe manufacture ofhydroxy stearic acid, (C17H3 C8%H) from oleic acid (C11H33 COOH,) withthe object of enhancing the economy in producing the first-namedsubstance by greatly increasing the yield thereof over that resultingfrom any known process hitherto practiced for the same purpose, withoutmaterially, if at all, increasing the expense involved in treating theoleic acid to be converted.

To practice my improved process in the best manner now known to me, Iproceed as follows: I first dilute the oleic acid to be treated with asuitable diluent, preferably a liquid hydrocarbon of the so-calledparaffin series, which is not acted upon by sulfuric acid, (H2SOi.)' Anydistilled petroleum may be used; but for the best results that of 60gravity Baume should be employed in the proportion of about two parts,by volume, to one part, by volume, of oleic acid. Other diluents,including any of the ethers or of the alcohols, may be used instead ofpetroleum, which, however, is preferred, though my invention is notintended to be limited thereto, for it consists, broadly, in the initialstep of diluting the oleic acid, with the result and advantage ofsubdividing it, and thereby exposing its particles extensively to theaction of the reagent employed for converting the oleic acid intosaturated oleic acid, which consti- .tutes the second step in myimproved process.

For this last-named purpose any reagent may be employed which exertswhat is known in chemistry as a polymerizing action, such as Zincchlorid, (ZnCl2;) but I prefer to employ sulfuric acid in the proportionof about one part, by weight, to three parts, by weight, of the oleicacid, which latter takes up the sulfuric acid and forms sulfo-oleicacid. Thus COOH and

- O0 O17H33COOH+ H2804 C17H3i (I) H2804.

The foregoing steps should be practiced under a low temperature, not toexceed, say, A0 Fahrenheit. The resultant product is then subjected tothe third step of the process, consisting in heating it with steamintroduced therein, with the effect of producing hydroxy stearic acid,thus primarily accomplishing my purpose, with the following reaction:

00 OH O17H3i H2O I os ogon acid treated, while by my improvement fullyone-half of such oleic acid is converted into bydroxy stearic acid. Thesolution containing the yield of hydroxy stearic acid, with thepetroleumand substances not acted on by sulfuric acid, is then separated from thesulfuric acid by allowing the steam-heated product to stand for an houror longer, whereby the weak sulfuric acid falls by its greater specificgravity to the bottom of the vessel in which the treatment is carried onand is drawn off and may be concentrated in any known or suitable mannerto recover it for use over again in the manner alreadydescribed.Thereupon hot petroleum naphtha in proportion about equal to thequantity of residual oils is added to the latter and dissolves the purehydroxy stearic acid and the other substances contained with it in themixture, or instead of the naphtha any of the alcohols or ethers orchloroform or any other suitable solvent may be used for this purpose.The solution is then cooled to about Fahrenheit, whereby the pure 11ydroxy stearic acid separates in white crystalline form, leaving behindthe other substances in solution in the solvent. The mixture isthereupon filtered to recover the crystals, which are then dried bysubjecting them to the action of a centrifugal drying-machine orotherwise, when they are ready for use. The naphtha or other solventemployed containing the other materials may be distilled off, leavingthem as a residue and recovering the naphtha to be used over again. Bythe procedure thus described about fifty per cent. of the oleic acidtreated is converted into hydroxy stearic acid, as aforesaid, and thiswithout material loss of the reagent and solvents employed. Theremainder of the oleic acid,

constituting about fifty per cent. thereof, has

been converted by the action of the reagent partially intostearo-lactone C17H3i the remainder being oleic acid unacted upon, andthese may be reconverted by distillation, the

oleic acid coming over through the tail-pipe of the still and beingsusceptible of treatment in the manner described to convert itintohydroxy stearic acid.

By thus subjecting the original charge of oleic acid to the treatment asdescribed, reconverting the residual presumed stearo-lactones into oleicacid, and subjecting the .latter again to the same treatment I recoverfrom, say, one hundred gallons of raw oleic acid a yield of abouteighty-five to ninety per cent. of hydroxy stearic acid as compared withtwenty-five to thirty per cent, which is the highest yield obtainable byother methods of treatment known to me.

hat I claim as new, and desire to secure by Letters Patent, is-

1. The process of manufacturing hydroxy stearic acid from oleic acid,which consists in diluting the oleic acid with a suitable diluent,converting the mixture to a saturated oleic acid by adding thereto asuitable polymerizing agent, and introducing steam into the resultantsolution, thereby converting the oleic acid into hydroxy stearic acid.

2. The process of manufacturing hydroxy stearic acid from oleic acid,which consists in diluting the oleic acid with a liquid hydrocarbon,converting the mixture to a saturated oleic acid by adding thereto asuitable polymerizing agent, and introducing steam into the resultantsolution, thereby converting the oleic acid into hydroxy stearic acid.

3. The process of manufacturing hydroxy stearic acid from oleic acid,which consists in diluting the oleic acid with a liquid hydrocarbon ofthe paraffin series, converting the mixture to a saturated oleic acid byadding thereto sulfuric acid, thereby forming sulfo-oleic acid, andintroducing steam into the resultant solution, thereby producing hydroxystearic acid.

4. The process of manufacturing hydroxy stearic acid from oleic acid,which consists 1n diluting the oleic acid with a suitable diluent,

converting the mixture to a saturated oleic acid by adding thereto asuitable polymerizing agent, introducing steam into the resultantsolution, thereby converting the oleic acid into hydroxy stearic acid,separating and withdrawing said agent, dissolving the hydroxy stearicacid by adding to the residual oils a suitable solvent, thereuponcooling the solution to reduce the pure hydroxy stearic acid tocrystalline form, and finally removing and drying the crystals.

5. The process of manufacturing hydroxy stearic acid from oleic acid,which consists in diluting the oleic acid with a liquid hydrocarbon,converting the mixture to a saturated oleic acid by adding thereto asuitable polymerizing agent, introducing steam into the resultantsolution, thereby converting the oleic acid into hydroxy stearic acid,separating and withdrawing said agent, dissolving the hydroxy stearicacid by adding to the residual oils a suitable solvent, thereuponcooling the solution to reduce the pure hydroxy stearic acid tocrystalline form, and finally removing and drying the crystals.

6. The process of manufacturing hydroxy stearic acid from oleic acid,which consists in diluting the oleic acid with a liquid hydrocarbon ofthe paraffin series, converting the mixture to a saturated oleic acid byadding thereto sulfuric acid,thereby forming sulfo-oleic acid,introducing steam into the resultant solution, thereby producing hydroxystearic acid, separating and withdrawing the sulfuric acid, dissolvingthe hydroxy stearic acid by adding to the residual oils a suitablesolvent, thereupon cooling the solution to reduce the pure hydroxystearic acid to crystalline form, filtering the solution to separate thecrystals, and drying the crystals.

7 The process'of manufacturing hydroxy stearic acid from oleic acid,which consists in diluting the oleic acid with a liquid hydrocarbon ofthe paraffin series, converting the mixture to a saturated oleic acid byadding thereto sulfuric acid,thereby forming sulfo-oleic acid, hydroxystearic acid to crystalline form, filterintroducing steam into theresultant solution, ing the solution to recover the crystals and therebyproducing hydroxy stearic acid, sepdrying the recovered crystals.

arating and Withdrawing the sulfuric acid, WILLIAM M. BURTON. dissolvingthe hydroxy stearic acid by adding In presence of to the residual oilshot petroleum naphtha, WALTER N. WINBERG,

then cooling the solution to reduce the pure L. HEISLAR.

